General “Jo” Shelby and His Great Raid through Missouri

By Mark Weaver

Joseph Orville Shelby, affectionately known as “Jo” Shelby, remains a captivating figure from the American Civil War. His reputation as a formidable cavalry commander is underscored by the high praise he received from both sides of the conflict. Union General Alfred Pleasonton, a man who had faced both Shelby and the famed Confederate cavalry leader General J.E.B. Stuart in battle, declared that "Shelby was the best cavalry general of the South. Under other conditions, he would have been one of the best in the world." This accolade is all the more significant considering Shelby’s lack of formal military training. He possessed an innate talent for warfare, a natural ability that led one biographer to describe him as a man who "fought like a man who invented fighting." Among his most notable achievements during the war was General “Jo” Shelby and His Great Raid through Missouri, a daring and impactful campaign that cemented his place in Civil War lore.

The backdrop to this audacious raid was the fraught environment of 1863, a time when Missouri, Shelby’s home state, was under Union control. In the autumn of that year, specifically on September 22nd, Colonel Jo Shelby departed from Arkadelphia, Arkansas. His objective was to penetrate Union lines and launch a raid into Missouri. Shelby’s motivation was fueled by his perception of the Union forces occupying Missouri. He viewed them as oppressors, characterizing them as "the terror to the country, the insulters of unprotected women, and the murderers of old and infirm men."

Shelby’s command, famously known as the "Iron Brigade," crossed into Missouri on October 2nd, marking the commencement of their ambitious operation. It wasn’t long before their presence became known. The initial target was Neosho, Missouri, a town Shelby knew was garrisoned by a detachment of Union troops. Employing a strategy of swift and decisive action, Shelby ordered his men to encircle the town, effectively cutting off any escape routes for the Union soldiers. With the town surrounded, the Iron Brigade launched a rapid assault. Shelby described the opening moments of the attack in vivid terms, noting that "the doomed enemy were encompassed by a cordon of steel before they knew of a foeman near. Thorp, with his usual dash, drove their pickets into town, where they, with the main body, took refuge in a strong brick court-house, pierced and loop-holed for musketry, where they kept up a hot fire upon our advancing columns."

Recognizing the Union troops’ entrenchment in the courthouse, Shelby deployed his artillery. "I ordered my cannon into position and sent two balls crashing through the walls," he recounted. The impact of the cannon fire was immediate. Faced with the prospect of further bombardment, the Union commander quickly requested terms. "This was followed by an immediate demand for unconditional surrender, which…they agreed to," Shelby stated. The capture of Neosho provided the Iron Brigade with a much-needed opportunity to rest and resupply. The success at Neosho set the tone for the early stages of General “Jo” Shelby and His Great Raid through Missouri.

From Neosho, Shelby’s men marched onward, their route taking them through the war-scarred landscape of Missouri. They passed through Sarcoxie, a town that bore the unmistakable marks of conflict. Shelby somberly described it as being "blackened and desolate." Continuing their advance, the Iron Brigade next seized Bowers’ Mill, further demonstrating their ability to overcome Union resistance.

The towns of Greenfield and Stockton soon fell under Shelby’s control. In these locations, the Iron Brigade "appropriated" supplies and arms from Union stores, replenishing their own resources while simultaneously depriving the enemy. They also systematically destroyed a fort in Stockton, eliminating a key Union stronghold in the area. The capture of these towns and the destruction of Union assets significantly disrupted Union operations in the region.

From Stockton, Shelby directed his forces towards Warsaw, a town strategically located on the Osage River. En route, they captured approximately 30 Union supply wagons, along with a number of Union soldiers. Upon reaching Warsaw, the Iron Brigade encountered resistance, but their superior numbers allowed them to quickly overwhelm the defenders. The capture of Warsaw proved to be a significant victory for Shelby, yielding a substantial amount of supplies and further bolstering the morale of his troops. However, Shelby recognized that the relative ease with which the raid had progressed thus far was unlikely to continue. He understood that the Union forces would soon mobilize to counter his advance.

Shelby prophetically noted that, "Vast quantities of all kinds of stores were captured here, with some arms and prisoners and a strong and well-provisioned fort. Thus far, I had traveled ahead of all information, but now the telegraph flashed out its view-halloo, and the railroads groaned under the dire preparations to meet me, and the thunderer of Saint Louis threatened vengeance as dark as death and terrible as the grave." His words conveyed an awareness that the Union response was imminent and that the challenges ahead would be far greater.

Over the next several days, Shelby and his men adopted a more deliberate pace as they moved through the towns of Cole Camp, Florence, Tipton, and Syracuse. They continued to capture supplies and arms, but also focused on disrupting Union infrastructure. They burned and destroyed numerous bridges and sections of railroad track, hindering the movement of Union troops and supplies. Furthermore, they systematically cut telegraph lines, disrupting communication and further isolating Union forces. The disruption of communication and transportation networks became a key element of General “Jo” Shelby and His Great Raid through Missouri.

The Iron Brigade eventually reached the Missouri River at Boonville. By this point, the "vengeance" Shelby had anticipated was indeed on its way, in the form of a large contingent of Union troops commanded by General Egbert Brown. Shelby, aware of the approaching threat, moved towards the town of Marshall. However, Brown cleverly divided his forces in an attempt to encircle Shelby and cut off his escape.

With Brown’s men closing in from both the front and the rear, Shelby made a strategic decision to split his own force, recognizing that it was the only way to break through the Union lines. The now-separated elements of the Iron Brigade managed to breach the Union encirclement in two different locations, demonstrating the skill and determination of Shelby’s men. The two units then retreated southward independently, each fighting to evade the pursuing Union forces.

The retreat was a grueling affair, with the Iron Brigade constantly harassed and pressured by their enemy. Finally, on October 26th, after weeks of relentless campaigning, Jo Shelby and the Iron Brigade managed to re-enter Arkansas, finding refuge behind Confederate lines. The completion of General “Jo” Shelby and His Great Raid through Missouri marked a significant, albeit costly, achievement for the Confederacy.

In his final report on the raid, Shelby claimed to have inflicted significant casualties on the Union forces, asserting that he had killed, wounded, and captured more than 1,000 Union troops. He also reported the capture and destruction of ten forts, as well as the capture, use, and destruction of Union supplies, property, and railroads valued at more than $2 million. While the accuracy of these figures may be debated, there is no doubt that Shelby’s raid had a substantial impact on Union operations in Missouri.

In recognition of his success, Shelby was promoted to Brigadier General. His daring and audacious raid quickly became legendary, inspiring a popular saying within the Confederate Army of the Trans-Mississippi: "You’ve heard of J.E.B. Stuart’s ride around McClellan? Hell brother, Jo Shelby rode around Missouri!" This comparison to Stuart, another renowned Confederate cavalry commander, underscored the magnitude of Shelby’s accomplishment.

General Jo Shelby continued to serve with distinction throughout the remainder of the Civil War. However, when the war drew to a close, Shelby and several hundred members of the Iron Brigade refused to surrender. Instead, they chose to ride into Mexico, where they established a "Gringo" colony, hoping to preserve their way of life. Unfortunately, their venture was short-lived, as the Mexican government was overthrown just two years later.

Shelby eventually returned to Missouri, where he spent many years engaged in farming. Later in life, he served as a U.S. Marshal for the final four years of his life, a remarkable turn of events for a former Confederate general. Prior to his appointment as a Marshal, Shelby’s testimony is believed to have played a significant role in the acquittal of the notorious outlaw Frank James.

Jo Shelby remains one of the most compelling figures of the Civil War. Despite lacking formal military training, he rose to become one of the most respected cavalry commanders of the conflict. His legacy continues to endure, and he and the men who accompanied him to Mexico are often remembered as "The Undefeated," a title that inspired a John Wayne movie purportedly based on Shelby’s story. His impact was deeply felt by those who served under him, as evidenced by the following verse:

Ho Boys! Make a Noise!
The Yankees are afraid!
The river’s up, hell’s to pay—
Shelby’s on a Raid!

© Mark Weaver, American Civil War Story, May 2013, updated June 2023.

About the Author: I’m Mark, and I have a website called American Civil War Story. Many people don’t realize how many fascinating Civil War stories they may be missing out on. My goal is to find as many of those great stories as I can and bring them together in one place for everyone to enjoy. On my site, you will find stories of Heroes, Spies, Battles, and Conspiracy. Don’t miss out!

Also See:

Civil War Main Page
Kansas-Missouri Border War
Missouri Civil War Battles
Warsaw, Missouri